5 Hard-Earned Lessons on Avoiding a Cash Flow Crunch in Your Life

While financial planning and good money stewardship are important, life is really short. So we’ve learned to celebrate successes along the way.

The Awakening

In 1996 my wife, Amy, and I were living out our version of the saying, “Life is what happens to you when you’re making other plans.”

We were adjusting to living on one income. Our first of three sons had arrived, and so, too, had come other surprises: we discovered our new health insurance didn’t cover well-baby visits, our central-air unit collapsed in the house we’d just bought, and we were spending through our savings to make everything work.

While all of this should have been a signal of our plight, it took Christmas morning that year for me to wake up to the reality of our finances.

As I unwrapped the pair of Nike Air Max running shoes Amy had gotten me, I did some quick math in my head. The glow of Christmas morning faded as I told her we had to return the shoes: we were broke.

This began a scramble to balance our cash flow: what bills could we pay and when could we pay them to be sure we had enough money to buy gas and groceries until my next paycheck?

From that memorable day, we made some changes that have led to financial freedom, and from among those changes, I offer five ideas as great steps to avoid the cash-flow scramble in your life:


My wife and I realized early in our now 28-year marriage that while we were deeply in love, we really didn’t know each other as well as we thought. (How does THAT happen?)

Too many exchanges between us started with, “But, I thought you were going to…, “I thought you wanted to …,” “I expected you to …”

We decided we needed a fresh approach to living together under one roof. That meant asking a lot more really clear questions about our goals, values, needs, and preferences, answering these with more honesty than at first felt comfortable and listening more closely to understand. (The tidal wave of emotions around the issue of money was startling to us.)

The result? Over time, we began to operate more on real facts rather than false assumptions, and we began to truly know each other better and the way forward for our lives. Clear communication is the heart of financial freedom in marriage.


One word about debt: don’t. It is so, so tempting today to just put everything you want on a credit card. Most offer incredibly high debt limits with exorbitant interest rates. (Experian reported in 2020, the average credit limit was a little more than $30,000….(WHAT?!) and that was a decrease from the prior year!)

It’s so tempting to just keep adding stuff onto the balance. But here’s what we’ve learned: debt is like a slovenly, drunken uncle who comes over for lunch, pushes you off your chair, eats your food, and then falls asleep on your couch until supper, only to wake up and start it all over again.

It will take decisive action and a “get-out-and-stay-out” attitude to get rid of the bum! Confiscate your credit cards and stop using them. Right. Now.


“The world is your oyster” is a beautiful thought, but it isn’t a great foundation upon which to build your financial life. What’s needed are specific, concrete, measurable goals, and outcomes that can, with their specificity, anchor your daily choices.

This means a budget, and a budget is simply a clear roster of where money is coming in and where it’s going out. It’s a list of proposed choices in a given month or year. It provides a roadmap to help you know when to say “yes” and when to say “no.” No lie: this takes real work and a focused time of truth-telling.

The concentration it takes to find a place for every dollar, every month is a deeply important investment. (Cue the fresh pot of coffee!)


Once the plan is in place, its true value is helping you measure your progress. How much are you spending on dining out? Was your car payment sent this month? What’s your trend in the cost to heat your home? Do you have enough money to fly to Cancun with your friends next week?

Keeping track of every dollar every week is a great way to avoid the deceitful mirage of unaffordable luxury. We use Tiller to manage our household finances and to keep an eye on our investments. This amazing tool gathers all of our financial transactions automatically and pulls them into a spreadsheet we can use to categorize and measure each against our budget. 

Each weekend, my wife and I try to have a “board meeting.” We look at the actual numbers of our budget and the built-in YTD progress reports for all our categories.

We discuss everything: what’s our savings goal, how much have we spent on groceries, why I have overspent on my allowance (again).

Every category has a target and we calibrate our future choices based on the facts.


Finally, we try to remember that while financial planning and good stewardship are important, life is really, really short. So, we’ve learned to celebrate successes along the way.

The big idea we’ve found is that it isn’t as much about what we want as it is about when we want it. Contrary to prevailing opinion, unless you’re independently wealthy, you simply can’t have everything you want when you want it. And if you think you can, you’ll never be independently wealthy.

Set goals to buy a house, buy a car, go to college, buy a business, change careers, go to Italy, and as you see progress happening toward each goal, celebrate, celebrate, celebrate. That’s awesome!

I have always been suspicious of people who offer formulas for life or five, quick steps to amazing happiness, so let me close with this: your journey may not look like ours, but there is still a journey for you to begin.

Which of these steps make sense to you or what additional ones would you add which speak to your soul’s desire for freedom? Simply begin today with one of those steps, and you’ll be on your way.

For us, it has made a world of difference. A well-designed tool like Tiller is essential.

We have greater peace and greater joy in life knowing we are the masters of our finances rather than the other way around.

And the best part? The next time I got running shoes for Christmas from my wife…

I got to keep ‘em.

Brad Warren

Brad Warren

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"There isn’t another tool on the market that does what Tiller can do.”
Will Hinton, Google Review October 30, 2023